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Preparation

Preheat oven to 350°F and line a muffin pan with cupcake liners. Twist Oreos in half and set aside the extra cookies for later. Place the side with cream filling in the bottom of each cupcake liner, cream-side facing up.
Place chocolate and cocoa in a medium bowl and pour the hot coffee over the mixture. Whisk until smooth and transfer to the refrigerator to cool completely, 20-30 minutes.
Whisk flour, sugar, salt, and baking soda together in a medium bowl; set aside.
Whisk oil, eggs, vanilla, and vinegar into the cooled chocolate mixture until smooth. Add flour mixture and whisk until batter is smooth.
Divide batter evenly among muffin pan cups, filling each 3/4 full. Bake until cupcakes are set and firm to the touch, 17-20 minutes. Allow to cool in pans 10 minutes, then transfer to a wire rack to cool completely before frosting.
For the frosting, in the bowl of an electric mixer fitted with the whisk attachment, combine the whipping cream, powdered sugar, and vanilla extract. Beat on medium-high speed until the whipped cream holds stiff peaks. Gently fold in the cooke crumbs with a spatula.
Scoop the mixture into a pastry bag and pipe on top of the cupcakes (I used a Wilton #1M tip for these cupcakes). Garnish with Oreo cookies.